4.8 Article

Nickel-Catalyzed Hydroamination and Hydroalkoxylation of Enelactams with Unactivated Amines and Alcohols

Journal

ORGANIC LETTERS
Volume 25, Issue 32, Pages 6093-6098

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c02341

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This study reports the nickel-catalyzed hydroamination and hydroalkoxylation reactions between unactivated amines and alcohols with enolactams. The method demonstrates good functional group tolerance and delivers the corresponding hydrofunctionalized products in good to excellent yields (& LE;98%). Additionally, an intramolecular hydroalkoxylation of an enolactam is successfully achieved, providing a cyclization product in good yield. Mechanistic studies reveal that tBuI plays crucial roles as a hydride donor and radical precursor for the reaction's success.
Nickel-catalyzedhydroamination and hydroalkoxylation of enelactamswith unactivated amines and alcohols are reported. This method showedgood functional group tolerance and delivered the corresponding hydrofunctionalizedproducts in good to excellent yields (& LE;98%). Furthermore, anintramolecular hydroalkoxylation of an enelactam was also realized,giving a cyclization product in a good yield. Mechanistic studiesindicated that tBuI acts as a hydride donor and radicalprecursor, which is crucial for the success of the reaction.

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